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I have been using Hiawatha on Windows (now v10) for several years without a single issue, I am thinking about moving my server to linux for additional flexibility and easy automated letsencrypt renewal.
I am not familiar with linux and would like to make it as easy and native as possible to integrate with Hiawatha. what distro would your recommend would Raspberry / Chrome OS require specific configuration or can I consider them as well
Thanks!

If you are not familiar with Linux, I advice to start with Ubuntu. It has many users and an active support forum. I don't know Chrome OS, but the Linux OS you are choosing won't affect how you configure Hiawatha.

I didn't manage to adapt your letsencrypt tool to Windows that was the reason why I was moving to Linux but I eventually managed to write in Windows a PowerShell script using the ACMESharp library that fully automates the LetsEncrypt certification . I can postpone my move to Ubuntu for the moment Thanks for your advice about Ubuntu I will look into it.